US5811833A - Electron transporting and light emitting layers based on organic free radicals - Google Patents
Electron transporting and light emitting layers based on organic free radicals Download PDFInfo
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- US5811833A US5811833A US08/774,120 US77412096A US5811833A US 5811833 A US5811833 A US 5811833A US 77412096 A US77412096 A US 77412096A US 5811833 A US5811833 A US 5811833A
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
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- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/302—Details of OLEDs of OLED structures
- H10K2102/3023—Direction of light emission
- H10K2102/3026—Top emission
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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
Definitions
- Organic light emitting devices have been shown to have sufficient brightness, range of color and operating lifetimes for use as a practical alternative technology to LCD-based full color flat-panel displays (S. R. Forrest, P. E. Burrows and M. E. Thompson, Laser Focus World, Feb. 1995). Furthermore, since many of the organic thin films used in such devices are transparent in the visible spectral region, they potentially allow for the realization of a completely new type of display pixel in which the red (R), green (G), and blue (B) emission layers are placed in a vertically stacked geometry to provide a simple fabrication process, minimum R-G-B pixel size, and maximum fill factor.
- red (R), green (G), and blue (B) emission layers are placed in a vertically stacked geometry to provide a simple fabrication process, minimum R-G-B pixel size, and maximum fill factor.
- tunable OLEDs utilize a blend of either two polymers (M. Granstrom and O. Inganas, Appl. Phys. Lett., vol. 68, 147 (1996)) or a polymer doped with semiconductor nanocrystallites (B. O. Dabbousi, M. G. Bawendi, O. Onitsuka and M. F. Rubner, Appl. Phys. Lett., vol. 66, 1316 (1995); V. L. Colvin, M. C. Schlamp, A. P. Allvisatos, Nature 370, 354 (1994)).
- Each component of the blend emits radiation having a different spectral energy distribution. The color is tuned by varying the applied voltage.
- a higher voltage results in more emission from the higher bandgap polymer, which emits radiation toward the blue region of the spectrum, while also resulting in higher overall brightness due to increased current injection into the device.
- tuning from orange to white has been demonstrated, incomplete quenching of the low-energy spectral emission appears to prohibit tuning completely into the blue.
- emission intensity can only be controlled by using pulsed current and reduced duty cycles. In a color display, therefore, prohibitively high drive voltages and very low duty cycles may be necessary for blue pixels. This necessitates a complex driver circuit, renders passive matrix operation extremely difficult, if not impossible, and is likely to accelerate degradation of the display.
- a transparent organic light emitting device which represents a first step toward realizing high resolution, independently addressable stacked R-G-B pixels has been reported recently in International Patent Application No. PCT/US95/15790 which corresponds to co-pending U.S. Ser. No. 08/354,674.
- This TOLED had greater than 71% transparency when turned off and emitted light from both top and bottom device surfaces with high efficiency (approaching 1% quantum efficiency) when the device was turned on.
- the TOLED used transparent indium tin oxide (ITO) as the hole-injecting electrode and a Mg-Ag-ITO layer for electron-injection.
- ITO transparent indium tin oxide
- a device was disclosed in which the Mg-Ag-ITO electrode was used as a hole-injecting contact for a second, different color- emitting OLED stacked on top of the TOLED.
- Each device in the stack (SOLED) was independently addressable and emitted its own characteristic color through the transparent organic layers, the transparent contacts and the glass substrate, allowing the entire device area to emit any combination of color that could be produced by varying the relative output of the two color-emitting layers.
- the color output produced by the pixel could be varied in color from deep red through blue.
- PCT/US95/15790 represents the first proof-of principle for achieving integrated, full color pixels which provide the highest possible image resolution, which is due to the compact pixel size, and low cost fabrication which is due to the elimination of the need for side-by-side growth of the different color-producing pixels.
- the subject invention is directed to electron transporting materials suitable for use in OLEDs wherein the electron transporting material is comprised of an organic free radical.
- the organic free radical comprises a multi-aryl-substituted cyclopentadienyl free radical, Cp Ar ., of formula (I): ##STR3## wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 each are, independently of the other Ar-groups, hydrogen, an alkyl group or an unsubstituted or substituted aromatic group.
- the subject invention is directed to an electron transporting material based on the pentaphenylcyclopentadienyl Cp.sup. ⁇ . free radical: ##STR4##
- the electron transporting material of the subject invention has the feature that an electron transporting layer can be prepared from an air-stable molecular precursor. Furthermore, the electron transporting layer can be prepared in vacuo from air stable precursor metallocene complexes. Still more specifically, in a representative embodiment of the subject invention, the electron transporting layers of the subject invention may be prepared from a Ge or Pb metallocene complex of Cp.sup. ⁇ ..
- a still further feature of the election transporting material of the subject invention is that the Cp.sup. ⁇ . complex may be readily reduced to the anion, giving the cyclopentadienyl ring aromatic character such that electron transfer from a cyclopentadienyl anion to an adjacent radical species is facilitated by overlap of the II-orbitals of the phenyl groups of adjacent molecules.
- the electron transporting material of the subject invention may be used to provide a good path for carrier transport through the material, resulting in an electron transporting layer (ETL) having especially beneficial properties, specifically including improved carrier mobility and carrier density, as compared to prior art materials.
- ETL electron transporting layer
- the electron emitting material may be selected from a family of chemical compounds that may also function as emissive materials, thus permitting the material to function in the dual role of an electron transporting material and of an emissive material.
- the chemical compound may be selected by adjusting the substituents in a manner such that the spectral emission has a color having a desired set of color coordinates as characterized, for example, by using the X-Y chromaticity coordinates of the CIE calorimetric system.
- the subject invention is directed, in a preferred embodiment, to an electron transporting layer that is included in a multi-layer structure having use as an electroluminescent device, wherein the electron transporting layer is comprised of an organic free radical and wherein the electron transporting layer is in electrical contact with a hole transporting layer. More specifically, the electron transporting layer is in direct physical contact with the hole transporting layer or is separated from the hole transporting layer by a layer containing an emissive material.
- FIG. 1 shows the side view of a representative single heterostructure incorporating an electron transporting material that may also serve as an emissive material.
- FIG. 2 shows the side view of a representative double heterostructure incorporating an electron transporting layer together with an additional layer which includes an emissive material.
- the electron transporting material of the subject invention is comprised of an organic free radical which may be readily prepared in a manner that is suitable for fabricating the electron transport layer of an OLED.
- the electron transporting material is represented by the chemical structure, Cp Ar ., of formula (I): ##STR5## which is herein referred to as multi-aryl-substituted cyclopentadienyl free radical, wherein each Ar-group, Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 , is hydrogen, an alkyl group or an unsubstituted or substituted aromatic group.
- Ar-group may typically be used to refer only to aryl groups, the term is used herein to include hydrogen or an alkyl group even though, preferably, at most only one of the Ar-groups is an alkyl group or hydrogen, with the remainder being the aromatic groups, and, most preferably, all of the Ar-groups are the aromatic groups.
- the aromatic groups may be independently selected to be the same or different, one from the other, with the total number of compounds that may be embraced by formula I being limited only insofar as they may be suitable for use in preparing an electron transporting layer and insofar as it is chemically practical to prepare such compounds.
- An organic free radical compound is herein defined to be suitable for use as an electron transporting material only if the carrier mobility of the electron transporting layer has a value of at least 10 -6 cm 2 /V sec.
- the unsubstituted or substituted aromatic groups may be, for example, phenyl groups; groups having fused phenyl rings, such as naphthyl; or aromatic heterocyclic groups such as pyridyl or thiophenyl.
- Each aromatic group may be, independently of the other aromatic groups, unsubstituted or substituted with one or more substituent groups.
- the substituent group, or groups may be an electron donor group, an electron acceptor group or an alkyl group.
- the unsubstituted or substituted aromatic group may be selected so as to adjust the spectral emission characteristics in a manner such as to produce a desired color, as characterized, for example, by using the X-Y chromaticity coordinates of the CIE calorimetric system.
- a desired color as characterized, for example, by using the X-Y chromaticity coordinates of the CIE calorimetric system.
- substantial changes in the emission spectra of a phenyl-containing compound may be produced dependent on whether the phenyl group is unsubstituted or is instead substituted in the orth or para position with an electron donor group or an electron acceptor group.
- the donor and acceptor groups may also be selected to affect the degree of intermolecular interaction and, thus, carrier mobility.
- substituents may also be selected so as to adjust the reduction potential of the organic free radicals, that is, the energy required to reduce the free radicals, thus converting the free radicals to the anions of the free radical.
- the carrier mobility and/or the carrier trap depth may be favorably altered, such that stable organic free radicals may be produced which have an overall combination of electrontransporting and electron-emissive properties that is particularly suitable for use as an electron transporting layer.
- the carrier mobility and carrier density of the heterostructure may be determined by measuring the I-V characteristics, for example, as described in P. E. Burrows et al, Applied Phys. Lett., vol. 64, 2285 (1994).
- the organic free radical is a pentaphenylcyclopentadienyl radical, Cp.sup. ⁇ . of formula (II): ##STR6## wherein each aryl group of formula (I) is defined in formula (II) as being a single phenyl group that may be unsubstituted, or substituted with the substituents R 1 , R 2 , R 3 , R 4 and R 5 , respectively, wherein each R-group represents independently from the other R-groups, one or more of an electron donor group, an electron acceptor group or an alkyl group.
- the organic free radical may be the unsubstituted Cp.sup. ⁇ . as represented by formula (III): ##STR7##
- the organic free radical may be the tetraphenylcyclopentadienyl free radical of formula (IV), ##STR8## and further-substituted variations thereof, for example, wherein the hydrogen shown in formula (IV) may be replaced by an alkyl group.
- the subject invention has the further feature that the substituents that are included in the organic free radicals may be selected so as to alter the emissive spectra and the reduction potential of the free radical in a manner so as to produce an overall combination of electron-transporting and electron-emissive properties that is particularly suitable for use as an electron transporting layer.
- the subject invention is thus directed to electron transport materials suitable for use in the electron transport layer of an OLED, wherein the electron transport material is comprised of a stable organic free radical having a readily accessible reduction potential between the stable organic free radical and the anion formed from the radical, for example, the pentaphenylcyclopentadienyl free radical, Cp.sup. ⁇ . , of formula (III) and the pentaphenylcyclopentadienyl anion of formula (V): ##STR9##
- a ready accessible reduction potential leads to suitable electron conduction through the electron transporting layer, wherein suitable electron conduction is herein defined to mean an electron conduction based on having an electron mobility of at least about 10 -6 cm 2 /V sec.
- An electron transporting layer comprised of the Cp.sup. ⁇ . free radical provides a further advantage in that the electron transporting material may, in some cases, also function as an emissive material in the OLED.
- the OLED may be fabricated using a single heterostructure, such as shown in FIG. 1. If the electron transporting material does not also serve as an emissive material, the OLED may be fabricated from a double heterostructure, such as shown in FIG. 2.
- the subject invention is directed toward a novel method for preparing the Cp.sup. ⁇ . free radical in bulk form as a thin layer of electron transporting material having a high electron mobility and a high electron carrier density, wherein the electron transporting layer is included in a multi-layer structure. It is believed that no prior art electron transporting materials have been disclosed which are comprised of an organic free radical.
- the subject invention is directed toward use of a multi-aryl-substituted cyclopentadienyl free radical, or more specifically, a multi-phenyl-substituted cyclopentadienyl free radical, or still more specifically, a pentaphenylcyclopentadieyl free radical as a species representing the preferred embodiment, it is to be understood that the subject invention is generally directed toward any organic free radical that may be contained in an electron transporting layer as an electron transporting material having an electron mobility of at least 10 -6 cm 2 /V sec.
- Cp.sup. ⁇ . free radical differs from the pentaphenylcyclopentadiene itself, Cp.sup. ⁇ H: ##STR10## in that Cp.sup. ⁇ H has been reported to be a blue emitting material when used in OLEDs, C. Adachi et al., Appl. Phys. Lett., vol. 56, 799-801 (1990), whereas a film of the pentaphenylcyclopentadienyl free radical has been observed and reported to have a purple color, M. J. Heeg et al., J. Organometallic Chem., vol. 346, 321-332 (1988).
- the Cp.sup. ⁇ . free radical differs from Cp.sup. ⁇ H in that the latter is not readily reduced. Reduction of Cp.sup. ⁇ H would have to be followed by loss of H + to give the stable anionic form, which is not energetically feasible. In particular, whereas there is no reason to expect, based on these differences, that Cp.sup. ⁇ H would have good carrier transport properties at all, the Cp.sup. ⁇ . free radical is capable of being especially well suited for this purpose.
- Cp.sup. ⁇ free radical material of the subject invention may be readily prepared in vacuo from air-stable precursor complexes.
- the purple films which are deposited from the gas phase organic free radical, Cp.sup. ⁇ . are comprised only of the Cp.sup. ⁇ . free radical material, according to Heeg et al.
- the subject invention is directed toward using such precursor materials and such methods to prepare electron transporting layers that may be used in substantially any type of multi-layer structure that includes an electron transporting layer.
- the free-radical-containing, electron transporting layer may be included, for example, in the multi-layer structure of a light emitting device.
- Such structures typically contain hole transporting layers, which may be in direct physical contact with the electron transporting layer, or alternatively, the hole transporting layer may be in direct physical contact with a layer of emissive material, which is in direct physical contact with the electron transporting layer.
- the layer of emissive material may be referred to as a luminescent layer.
- the hole transporting layer is comprised of a material that is typically described as providing electrical conduction, when a voltage is applied, preferentially by the conduction of holes, as distinct from the electron transporting layer that provides electrical conduction preferentially by the conduction of electrons.
- the subject invention is, thus, directed to incorporating the subject electron transporting layers into multi-layer structures wherein the electron transporting layer is in electrical contact with a hole tranporting layer.
- the stable organic free-radical-containing materials are intended to provide benefits and advantages that are uniquely suited for use as an electron transporting material, when such free-radical-containing materials are incorporated into a multi-layer structure as the electron transporting layer. While it is intended, in the more preferred embodiments of the subject invention, that the electron transporting layer be comprised predominantly of an organic free radical, or even, in some cases, be directed to electron transporting layers consisting essentially of organic free radicals, it is also contemplated that layers containing free radical materials that have undergone dimerization, even substantial dimerization, may also serve as effective electron transporting materials, and are, therefore, also contemplated to fall within the scope of the subject invention.
- the electron transporting layer be comprised predominantly, if not completely, of an organic free radical material
- the subject invention is intended to embrace any electron transporting layer that includes an organic free radical material for which it can be shown that the presence of the organic free radical contributes to the electron transporting characteristics of the electron transporting layer.
- the layer may be comprised of organic free radical materials that are embedded in a matrix of non-free-radical, but still electron transporting, material.
- An electron transporting layer comprised predominantly of an organic free radical is herein defined as a layer in which the organic free radical is the major component of the electron transporting layer.
- the Ge (decaphenylgermanocene) or Pb (decaphenylplumbocene) complex of pentaphenylcyclopentadienyl is used as the source for preparing the thin layers of Cp.sup. ⁇ . in a vacuum deposition system.
- the subject electron transporting materials may be incorporated into a single heterostructure as schematically illustrated in FIG. 1 or in a double heterostructure as schematically shown in FIG. 2.
- the materials, methods and apparatus for preparing the single and double heterostructures are disclosed, for example, in U.S. Pat. No. 5,554,220, which is herein incorporated in its entirety by reference.
- These structures are intended solely as examples showing how a multi-layer structure embodying the subject invention may be fabricated without in any way intending the invention to be limited to the particular sequence or order of making the layers shown.
- FIG. 1 shows a multi-layer structure for which the sequence of layers, which are in direct physical contact, includes a substrate 1, which is preferably transparent, for example, glass or plastic; a first electrode, which may typically be an indium tin oxide (ITO) anode layer 2; a hole transporting layer 3; an electron transporting layer 4; a second electrode layer 5, for example, a metal cathode layer of Mg:Ag; and a metal protective layer 6, for example, made of a layer of Ag, for protecting the Mg:Ag cathode layer from atmospheric oxidation.
- FIG. 2 shows an additional layer 7, which includes an emissive material.
- the ITO anode layer may be about 1000 ⁇ to greater than about 4000 ⁇ thick; the hole transporting layer about 50 ⁇ to greater than about 1000 ⁇ thick; the layer containing emissive material, layer 7, about 50 ⁇ to about 200 ⁇ thick; the electron transporting layer about 50 ⁇ to about 1000 ⁇ thick; and each metal layer, layers 5 and 6, about 50 ⁇ to greater than about 100 ⁇ thick, or substantially thicker if the cathode layer is not intended to be transparent.
- the electron transporting layers comprised of organic free radicals may be included in substantially any type of multi-layer structure containing an electron transporting layer, for example, in multi-layer structures that are used to make an electroluminescent device, which is then incorporated into another device, such as a light emitting display device that is then incorporated into a larger display, a vehicle, a computer, a television, a printer, a large area wall, theater or stadium screen, a billboard or a sign.
- ITO indium tin oxide
- the substrate may be ultrasonically cleaned in detergent, followed by thorough rinsing in deionized water, 1,1,1-trichloroethane, acetone and methanol, and dried in pure nitrogen gas between each step.
- the clean dry substrate is then transferred to the vacuum deposition system. All organic and metal depositions may then be carried out under high vacuum ( ⁇ 2 ⁇ 10 -6 Torr). Depositions are carried out by thermal evaporation from baffled Ta crucibles at a nominal deposition rate of 2-4 ⁇ /s.
- an approximately 350 ⁇ layer 3 of N,N'-diphenyl-N,N'-bis(3-methyphenyl)-1,1-biphenyl-4,4'-diamine (TPD) may be vapor deposited on the cleaned ITO substrate.
- a sample of M(C 5 Ph 5 ) 2 (where M may be Ge or Pb) may then be heated to ca. 250° C., liberating Cp.sup. ⁇ . , which may be deposited on top of the TPD film as layer 4.
- the final thickness of the Cp.sup. ⁇ . film may be about 400 ⁇ .
- An array of circular 250 mm diameter 1,000 ⁇ electrodes 5 of approximately 10:1 Mg:Ag atomic ratio may be subsequently deposited by coevaporation from separate Ta boats.
- a 500 ⁇ thick layer 6 of Ag may be deposited to inhibit atmospheric oxidation of the electrode.
- a double heterostructure such as shown in FIG. 2, may be fabricated by including the emissive layer 7, which may be formed as doped or un-doped tris-(8-hydroxyquinoline) aluminum Alq 3 : ##STR13##
- FIG. 2 shows an Alq 3 layer which is un-doped, thus functioning as an intermediate hole-blocking and recombination/emitting layer.
- the double heterostructure shown in FIG. 2 is prepared substantially as described for the single heterostructure structure, except that after depositing the TPD layer 3 and before depositing the organic free radical layer 4, layer 7, which is formed from Alq 3 is deposited.
- the subject invention may also be used in conjunction with the subject matter of co-pending U.S. Ser. Nos. 08/354,674; 08/613,207; 08/632,316; 08/632,322; 08/693,359; 60/010,013; and 60/024,001; which are also herein incorporated in their entirety by reference.
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Abstract
Description
MX.sub.2 +2 Cp.sup.φ Li→(Cp.sup.φ).sub.2 M+2LiX, (1)
Claims (29)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
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US08/774,120 US5811833A (en) | 1996-12-23 | 1996-12-23 | Electron transporting and light emitting layers based on organic free radicals |
KR1019997005719A KR20000062301A (en) | 1996-12-23 | 1997-12-23 | An organic light emitting device containing a protection layer |
CA002275542A CA2275542A1 (en) | 1996-12-23 | 1997-12-23 | An organic light emitting device containing a protection layer |
PCT/US1997/023952 WO1998028767A1 (en) | 1996-12-23 | 1997-12-23 | An organic light emitting device containing a protection layer |
JP52908098A JP2001527688A (en) | 1996-12-23 | 1997-12-23 | Organic light emitting device containing protective layer |
EP97953470A EP0950254A4 (en) | 1996-12-23 | 1997-12-23 | An organic light emitting device containing a protection layer |
CN97181500A CN1245581A (en) | 1996-12-23 | 1997-12-23 | Organic light emitting device containing protection layer |
AU57210/98A AU5721098A (en) | 1996-12-23 | 1997-12-23 | An organic light emitting device containing a protection layer |
US09/025,660 US5922396A (en) | 1996-12-23 | 1998-02-18 | Electron transporting and light emitting layers based on organic free radicals |
TW86119632A TW385620B (en) | 1996-12-23 | 1998-03-07 | An organic light emitting device containing a protection layer |
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Cited By (101)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5989737A (en) * | 1997-02-27 | 1999-11-23 | Xerox Corporation | Organic electroluminescent devices |
WO2000065879A1 (en) * | 1999-04-28 | 2000-11-02 | Emagin Corporation | Organic electroluminescence device with high efficiency reflecting element |
WO2001013683A1 (en) * | 1999-08-16 | 2001-02-22 | The University Of Southern California | Cyclooctatetraenes as electron transporters in organic light emitting diodes |
US6242115B1 (en) | 1997-09-08 | 2001-06-05 | The University Of Southern California | OLEDs containing thermally stable asymmetric charge carrier materials |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
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